Los Angeles (LAX) to Chicago (MDW) flight deal in economy from $99
LAXLos Angeles International Airport
Los Angeles, United States
MDWMidway International Airport
Chicago, United States
$186 USD
-47%$99 USD
Verified about 2 hours agoOctober 2026
Mon
Tue
Wed
Thu
Fri
Sat
Sun
Extremely Rare Availability
4% of dates checked are available within 10% of the lowest price
Saturday, October 31st, 2026
Outbound Flights
3h 50m·Nonstop
$99 USD
LAXOct 31 06:05
→MDWOct 31 11:55
WN 1627Boeing 737MAX 8 Passenger
3h 50m·Nonstop
$99 USDLAXOct 31 11:55
→MDWOct 31 17:45
WN 3473Boeing 737-700 (Scimitar Winglets) Pax
5h 25m·1 stop
$109 USDLAXOct 31 08:15
→STLOct 31 13:45
WN 3406Boeing 737MAX 8 Passenger
50m layover
STLOct 31 14:35
→MDWOct 31 15:40
WN 2721Boeing 737MAX 8 Passenger
6h 15m·1 stop
$109 USD
LAXOct 31 09:45
→DTWOct 31 17:09
DL 494Airbus A321neo
31m layover
DTWOct 31 17:40
→MDWOct 31 18:00
DL 4677Canadair RJ 700
6h 10m·1 stop
$109 USDLAXOct 31 07:15
→DALOct 31 12:15
WN 2858Boeing 737MAX 8 Passenger
55m layover
DALOct 31 13:10
→MDWOct 31 15:25
WN 910Boeing 737
5h 30m·1 stop
$109 USDLAXOct 31 09:20
→PHXOct 31 10:45
WN 1640Boeing 737MAX 8 Passenger
50m layover
PHXOct 31 11:35
→MDWOct 31 16:50
WN 2896Boeing 737MAX 8 Passenger
5h 25m·1 stop
$189 USDLAXOct 31 06:45
→DENOct 31 10:00
WN 2863Boeing 737
50m layover
DENOct 31 10:50
→MDWOct 31 14:10
WN 1090Boeing 737
8h 18m·1 stop
$199 USDLAXOct 31 12:15
→ATLOct 31 19:30
DL 395Airbus A321neo
2h 9m layover
ATLOct 31 21:39
→MDWOct 31 22:33
DL 1076Airbus A319
9h 52m·1 stop
$199 USDLAXOct 31 23:55
→ATLNov 1 06:12
DL 579Airbus A321neo
3h 38m layover
ATLNov 1 09:50
→MDWNov 1 10:47
DL 1063Airbus A320